Synthesis of ethyl chlorooxoacetate

Preparation of ethyl chlorooxoacetate

Preparation of ethyl chlorooxoacetate

Preparation of ethyl chlorooxoacetate

A mixture of phosphorus pentachloride (2 kg; powdered immediately before use) and diethyl oxalate (1.8 kg) is heated at 95-100° for 4 days with exclusion of moisture. The reaction time can be shortened by shaking. Phosphorus oxychloride (b.p. 27°/18 mm) is then distilled off in a vacuum, and the residue is heated with palladium black (0.5 g) at 95-98°, until no more ethyl chloride is split off (2 hours), and it is worked up by vacuum-distillation. The yield of ethyl chlorooxoacetate is 1150 g, b.p. 39.7°/18 mm.

R. Scholl, W. Egerer, Ann. Chem., 397, 326 (1913).

L.Bert, R. Barre, Bull Soc. Chim. France [iv], 37, 1041 (1945); 41, 47, 1165 (1927).

IUPAC Name

ethyl 2-chloro-2-oxoacetate

InChI

InChI=1S/C4H5ClO3/c1-2-8-4(7)3(5)6/h2H2,1H3

InChI Key

OWZFULPEVHKEKS-UHFFFAOYSA-N

Canonical SMILES

CCOC(=O)C(=O)Cl

MeSH Synonyms

ethoxalyl chloride

Depositor-Supplied Synonyms

Ethyl oxalyl chloride, Ethyl chlorooxoacetate, ETHYL CHLOROGLYOXYLATE, 4755-77-5, Ethoxalyl chloride, ethyl oxalyl monochloride, Ethyl 2-chloro-2-oxoacetate, Oxalic acid monoethyl ester chloride, Ethyl (Chlorocarbonyl)formate, Acetic acid, chlorooxo-, ethyl ester, ethyl chloro(oxo)acetate, Monoethyl oxaloyl chloride, mono-Ethyl oxalyl chloride, Oxalyl chloride, ethyl ester, Chlorooxalic acid ethyl ester, ethyl 2-chloro-2-oxo-acetate, chlorooxoacetic acid ethyl ester, Chloroglyoxylic Acid Ethyl Ester, MFCD00000706, Monoethyl oxalyl chloride, Acetic acid, 2-chloro-2-oxo-, ethyl ester, ethoxalylchloride, ethylchlorooxalate, ethyl chlorooxalate, ethylchlorooxoacetate, Ethoxy oxalylchloride, ethyl chloroglyoxalate, Ethylchlorooxo-acetate, ethyl chloro-oxoacetate, ethylchloro(oxo)acetate, ethyl chloroformylformate, ethyl chloro-oxo-acetate, ethyl chloroglyoxylic acid, ethyl chloro-(oxo)acetate, chloroglyoxylic ethyl ester, ACMC-209k9u, ethyl (chloroformyl)formate, AC1L2H6R, SCHEMBL23824, E43101_ALDRICH, KSC489Q8B, chloro-oxalic acid ethyl ester, AC1Q324D, DTXSID3063598, 75753_FLUKA, CTK3I9880, OWZFULPEVHKEKS-UHFFFAOYSA-N, BB_SC-6434, chloro-oxo-acetic acid ethyl ester, NSC80644, ZINC1639557, EINECS 225-285-0, ANW-30544, BBL027307, NSC 80644, NSC-80644, STL371945, ZINC01639557, Glyoxylic acid, chloro-, ethyl ester, 2-chloro-2-oxoacetic acid ethyl ester, AKOS000120204, MCULE-6454421959, RP20303, AN-19067, BP-13267, OR038368, OR272691, ethyl 2-chloranyl-2-oxidanylidene-ethanoate, TR-017527, X4976, A827270, I14-0327, F2190-0031

Removed Synonyms

Acetic acid, ethyl ester, C4H5ClO3, Glyoxylic acid, ethyl ester, MolPort-000-160-180, CID20884, c1066, RTR-017527

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